Reaktion #578885

Reaktionsgleichung

2,5-dimethoxyaniline

triethylamine

2,5-dimethoxybenzoic acid

thionyl chloride

HCl

→

solid

Ausbeute 93.0%

N-(2,5-Dimethoxyphenyl)-2,5-dimethoxybenzamide

Ausbeute 93.0%

Lösungsmittel

THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 1 h
2. 2
   SonstigeThe volatiles were removed under vacuum
3. 3
   workup.DISSOLUTIONThe residue was dissolved in THF (20 mL
4. 4
   Extraktionextracted with EtOAc
5. 5
   TrocknenThe organic extracts were dried over MgSO4
6. 6
   SonstigeEvaporation and purification by flash chromatography (hexanes/EtOAc 2/1)

Vorschrift

A mixture of 2,5-dimethoxybenzoic acid (5.0 g, 27.5 mmol) and thionyl chloride (15 mL) was refluxed for 1 h. The volatiles were removed under vacuum. The residue was dissolved in THF (20 mL and added into a cold (0° C.) solution of 2,5-dimethoxyaniline (4-6 g, 30.2 mmol), triethylamine (5 mL, 35.9 mmol) and THF (40 mL). The mixture was stirred for 30 min, poured into water, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 2/1) gave a white solid (8.1 g, 93% yield, m.p. 121-123° C.); MS m/e 318 (M+H)+.

Quelle